Polymerization of vinyl naphthalene



Patented Doc. 4.1

PATENT orrice 1,982,676 POLYMERIZATION or vmrr. NAPHTHALENE' Walter E. Lawson,

Wilmington, Del., assignor to v E. I. du Pont de Nemours & Company, Wilmington,.Del., a corporation of Delaware \No Drawing.

Application August 21, 1929,

Serial No. 387.588

s Claims.

This'invention relates to new compositions of matter formed by the polymerization of vinyl naphthalene. More specifically this invention relates to new compositions of matter useful in a molding compositions and lacquers. It furthermore relates to a method of polymerizing vinyl naphthalene.

The object of the invention is the production of a new and improved composition of matter.

A still further object is the use of vinyl naphthalene in the preparation of material useful as a lacquer'constituent, and a still further object is to discover means of polymerizing vinyl naphthalene.

These objects are accomplished by the follow ing invention which consists in the polymerization of vinyl naphthalene by the'application of heat, or by catalysts, or by the combination of catalysts and heat.

I have found that both the alpha and beta forms of vinyl naphthalene are readily polymerized by heat alone, by catalysts, or by catalysts and heat to yield polymers which are valuable as resins, are valuable in the preparation of varnishes and lacquers, and for the other purposes for which resins are used. The catalysts which I have found most useful are metallic chlorides, and peroxides.

In the examples below is set forth the generalmethod of procedure whereby the new compositions of matter are formed. After the polymerization has taken place I separate out the polymer and treat it in the manner appropriate to the use to which it is to be put. If it is to be usedas a lacquer it is dissolved in a suitable solvent such as aromatic hydrocarbons and their substituents, such as toluene, xylene, ethyl benzene, and their halogen substitution products, etc., or their mixtures may be used as solvents; esters, such as methyl acetate, ethyl acetate, etc., may also be employed. Alcohols as a class are nonsolvents and tend to precipitate the resin from its solutions.

Example 1 Example 2 A sample of vinyl naphthalene in ethyl bemzene solution was heated with two percent of benzoyl peroxide for three hours at 100 to 120 C. A fifty percent yield of polymer was obtained. Films from this resin were slightly tacky after two hours drying, but were hard dry in live hours at room temperature. 00

Example 3 Example 4 A lacquer was made from the following formula and gave a hard tough finish that aged for one 10 year without cracking or checking.

, Parts Polyvinyl naphthalene 25 Solvent (toluene xylene 50%) An advantage of this process is that vinyl naphthalene is made useful as the base from which to get polymerizationproducts. A further advantage is that the polymer is of a light color.

A still further advantage is that the extreme so solubility of these resins in cheap solvents, and their insolubility in alcohol are exceptionally valuable from the standpoint of automobile finishes.

A still further advantage is that since aromatic hydrocarbons can be used for solvents the solvent cost is considerably lower than for cellulose ester finishes.

It will be apparent from the listed examples that very wide variations in temperature are possible without detracting from the utility of I the process.

Although specific examples of the process have been given, it is to be observed that many varia- I tions which will occur to persons skilled in the art can be made without departing from the legiti mate scope of the invention. The invention is not to be construed as limited except as by the appended claims.

I claim:

1. Polymerized vinyl naphthalene.

2. The method of polymerizing vinyl naphtha lene which comprises heating vinyl naphthalene to a temperature above atmospheric temperature and below the point of decomposition of the vinyl naphthalene.

3. The method of polymerizing vinyl naphtha lene comprising the heating thereof to approximately 300 C.

4. The process of making polymerization prod ucts from vinyl naphthalene comprising heating m a solution containing vinyl naphthalene to a temperature above atmospheric temperature but below the temperature of decomposition of vinyl naph ilglalene.

5. e process as in claim vent used is ethyl benzene.

6. The method of making polymerization prodnets of vinyl naphthalene comprising dissolving vinyl naphthalene in a solvent, and heating to a temperature above atmospheric, but below the temperature at which the solution is volatilized.

7. The method of making polymerization prodnets of vinyl naphthalene comprising the solution of vinyl naphthalene in a solvent comprising ethyl benzene which contains benzoyl peroxide, and the heating thereof to a temperature of approximately 115 C.

8. The method of polymerizing vinyl naphthalene comprising treating it with a polymerization catalyst of the group consisting of benzoyl peroxide and stannic chloride.

9. The method of polymerizing vinyl naphthalene which comprises heating vinyl naphthalene above atmospheric temperature but below the decomposition temperature of vinyl naphthalene 4 in which the solin the presence of a catalyst from a group consisting oi benzoyl peroxide stannic chloride.

10. The method of making polymerized prod-'- ucts of vinyl naphthalene which comprises heating vinyl naphthalene to a temperature between about 100 C. and about 300 C.

11. The method of making polymerized prodnets of vinyl naphthalene which comprises heating vinyl naphthalene between about 100 C. and about 120 C.

12. The method of polymerizing vinyl naphthalene which comprises heating vinyl naphthalene 

